


RoseGarden Week 2019

by Imawriteritswhatido



Category: RWBY
Genre: Adult Entertainer AU, Aged up characters, Crossposted on my Tumblr, F/M, Historical AU, more AUs to come, will update tags accordingly - Freeform
Language: English
Status: In-Progress
Published: 2019-10-28
Updated: 2020-01-01
Packaged: 2021-01-05 20:47:00
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,905
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21214826
Author URL: https://archiveofourown.org/users/Imawriteritswhatido/pseuds/Imawriteritswhatido
Summary: RoseGarden Week...Ah, RoseGarden Week...Look, it's RoseGarden Week, okay, and I wanted to participate. Enjoy.





	1. 🌹 October 27th: Crossroads/Free Day

Free days were always something intimidating to Oscar.

When he was on the farm, there was a strict regimen of chores to do; planting, picking, milking, gathering eggs, plowing, weeding…

Looking back on it, it felt far enough away to make his head spin, even though it was only a month into the past.

Life moved fast when you were fighting for your life.

But now that he was…whatever he was now, there was no schedule, no to-do list, just an obscene amount of free time.

Weiss seemed pretty well-put together. Maybe she could give her some tips about what to do about free days like this.

He’d asked Blake and she’d said she measured time and accomplishment by the books she read. Scheduling around a book list seemed interesting.

Yang didn’t seem to care either way, just rolling with the punches. She seemed to like punches.

“Come on, Oscar!”

But when she grabbed his hand and yanked him off into the unknown, freewheeling and utterly happy to be among the people she thought of as friends, when she blanched at some unknowable that made itself known at the last second, the decisions didn’t seem as daunting.

Ruby Rose was someone people could follow into battle, and then follow out of battle.

Sometimes, she would see him doing something related to his previous existence as a farmer and join him (it was adorable watching her try to pull a stubborn weed that was actually a carrot out of the ground).

Sometimes, she would offer him a round of video games and when she smiled like that, who was he to deny her.

Sometimes, free days came with too many options.

Other times, they just came with Ruby and those were probably Oscar’s favorite days.


	2. 🌹 October 28th: Stars

**Notes for the Chapter:**

> This is so, so late it's not even funny. But, enjoy guys

“Are…Are we sure this is appropriate?”

That was probably the fifth or sixth time Oscar had asked that. This night alone, that is.

The woman applying makeup to his face rolled her eyes and applied the second fake sideburn to the side of his face.

“Yes, it’s appropriate,” she said, “We’ve checked you out for STDs from head to toe. You’re clean.”

“It’s not that,” Oscar said, fidgeting in his seat, “it’s just…”

He turned around and faced the mirror on the dressing room vanity.

“What if…what if someone I know sees this?”

The woman sighed.

“It’s not going to come to that.” she put her hand on his shoulder, “this film will be for your private collection. It won’t be advertised on our website or released on the internet in any way. We’re not that kind of company.”

Oscar looked at her with a raised eyebrow.

“If you’re worried about having a job after this, I do make up for major motion pictures.”

“Really?”

“I was a student of Rick Baker.”

“The werewolf guy?”

“That’s right. Now, hold still while I give you your unibrows.”

Oscar wasn’t entirely sure why he needed them. Sideburns, unibrows, and yellow contacts certainly didn’t seem like something the star of an adult video would wear.

“If you’re wondering about the makeup, our director is pretty…”

The woman paused, probably trying to find the appropriate word.

“Out there.”

“Oh.”

“She used to be a performer herself.”

“Really?”

“Yeah, she still takes parts from time to time. But mostly she just directs and produces now.”

“What about you?”

“Hmmm…?”

“Are you a… an adult performer, too?”

“Yep. Worked with the director a few times before, too.”

“Really? You just seem so…so…”

“Normal? Sure. Just because I like to wear cat ears while getting ploughed doesn’t mean I don’t have a life outside of it.”

Oscar’s eyes widened. He wasn’t an aficionado, but he knew one star that had cat ears as a gimmick.

“You’re Kitty Loggins!”

The woman smiled.

“Not when I’m off camera. Here, I’m just Blake Belladonna.”

“Oh,” Oscar said, “well, it’s nice to meet you, Blake. I’m Oscar.”

“Nice to meet you too Oscar.”

The woman finished gluing the fake hair between his eyebrows and reached for a triangular piece of fabric that looked suspiciously like an animal ear.

“Almost done, just hold still for a moment.”

The people of the Beacon Adult Entertainment had been nothing but nice to him the whole time he’d been here. A far cry from the temple of debauchery he was expecting when he’d gotten here.

But still…

He’d entered the contest as a joke!

Enter now to win a shoot and a day with a Pornstar, the digital flyer had read in big carnival-style font. He was sure it was just a scam or something in that ballpark, since it had appeared in the part of his inbox marked as spam. He’d signed on the dotted digital line and beefed up his virus protection. In two weeks, he and his friends would be laughing about it, no sweat.

But a week and a half later, it had come in the mail.

Congratulations to our new winner, it said in gold foil, you’ve won an all-expenses paid trip to Los Angeles to spend a day with one of our performers at Beacon Adult Entertainment.

He’d almost choked when he finished reading the pass. What would his Aunt say?

It wasn’t like he was a regular patron of the salacious screen stories. Most of the time, it was just that he had to scratch an itch and he bought a dirty magazine with some of the money he’d saved up or watch a video online.

If she found out he’d entered a porn-related contest, even as a joke…

It had taken every bit of his guile and not inconsiderable innocent act to get his aunt to think he’d just won a vacation with no porn involved.

Now, she was asleep in a four star hotel across town while he was sitting in a studio dressing room, getting ready to have sexual intercourse with a total stranger. Thank God the BAE Agency had sent them a personal car and he hadn’t had to tell cab ‘can you take me to the place where they shoot porn?’

It’s not like he couldn’t back out. Nothing in the contest guidelines said that he couldn’t.

But going home meant they’d have to go leave so soon, his Aunt would get suspicious and that meant he might have to come clean to her about how he won this vacation.

“All done,” Blake said, turning Oscar around in his chair so he was facing the mirror, “what do you think?”

In all honesty, it wasn’t bad. He still looked like him, just a little hairier. And the false ears gave him a wolfy appearance.

“It’s pretty good.”

“I do my best. But you might want the brace yourself.”

Blake walked to the other side of the room and took a book from out of her bag.

“The director should be here any minute?”

Oscar frowned.

“Why would I need to brace—“

** “Hell-ooo!” **

A tall woman with a pair of aviator sunglasses and blonde hair as generous as her busom burst into the room with a sing-song shout. Judging by the t-shirt that read ‘trust me, I’m a director’ Oscar could probably guess who this was.

“So where’s our newest star?”

Blake pointed to where Oscar sat and the boy shrunk as the woman gazed at him from over the tip of her sunglasses.

“Well, aren’t you just the cutest little thing.”

The director pinched his cheek and Oscar felt the distinct need to commit seppuku.

“And, I think I have just the girl for you.”

“Yang,” Blake sighed, “Don’t do this again.”

“Do what?”

“This whole…matchmaker thing. Winter almost quit because of you.”

“But she didn’t.”

“I’m still surprised she and Qrow didn’t kill each other.”

“John Boorman did the same thing on Excalibur with Nicol Williamson and Helen Mirren.”

“Boorman didn’t need his actors to have sex with each other.”

The woman, Yang, waved her hand dismissively.

“Details, details…”

Yang grabbed (as in, physically picked him up like a package) Oscar and sat him down in the hallway.

“So, kid, you ready to get your mind blown?”

“No.” Oscar said, only half sure that was his answer.

“Perfect!” Yang said, ushering him in the direction of what he assumed was the set.

“I know you’re nervous,” she said, “that’s natural. You read the script?”

“Yeah, it’s…”

“Garbage, I know. Just give it your all and don’t worry about how you look. And before I forget, here’s your stage name. We were a little short on time, but I think we came up with something that suits you.”

The director, Yang, handed him what looked like a business card, which Oscar took. Half a second later, he stared at her, incredulous.

“Pino Largo!?”

“Oh, come on!” Yang said, slapping him on the back, “Everyone has names like that in this biz.”

“But why do I need a stage name? You’re not releasing this!”

Yang stopped and turned to look at him, confused.

“We’re not?”

Oscar shook his head.

“No!”

Yang recovered in record time.

“Well, we didn’t advertise a new release anyway. No skin off our nose.”

* * *

The story was simple. A filthy take on little red riding hood where Little Red fucked the wolf’s brains out. Oscar was just thankful he didn’t have to wear an old lady nightgown for his part. Just be ruefully naked under the sheets in a room full of people in a mock woodland cottage bedroom.

He shivered.

Did Yang have to pick a filming locale that was so drafty? If it wasn’t for the bedclothes, he’d be freezing his butt off.

“Sorry I’m late!”

A voice off to Oscar’s left caught his ear and he turned to see who it was. It sounded familiar.

Oscar turned his head enough to see a woman in a red jacket was hugging Yang. When she finally pulled away, Oscar could see her face.

Ruby Rose.

He was shooting a porno with Ruby Rose.

Suddenly, Oscar’s throat felt like a desert and his stomach like a butterfly habitat.

Of all the adult actresses he would have to appear in a film with, it had to be with the one he’d been crushing on since the first time he’d seen her in the swimsuit issue of a magazine!

When Oscar had told himself that he didn’t follow adult entertainment, he may not have been being completely honest with himself.

With her petite cutie pie looks and Hot Topic style, she was easily the most gorgeous creature he’d ever seen. Plus, she was always so funny in her videos and make-up videos. And she also knew karate, so that was kind of cool. And also…

“Ruby! Come meet your co-star!”

Damn that crazy director! Now they were coming this way.

Just play it cool, thought Oscar, It’s no big deal, it’s just the beginning of the end of your life.

Oscar tugged the covers up over his face so that his eyes were the only thing visible. He could just say he was method acting.

“Ruby, this is Pino. He’s the one who won the contest. Say hi, Pino.”

Oscar looked up at Ruby, sweet smiling and in no way sexual. Great, not only was she sexy, she was cute and just…

Say something Oscar, he thought, anything!

“You…you have silver eyes…”

Anything but that! Ruby frowned, obviously confused.

“They’re contacts for the shoot.”

Oscar didn’t have time to apologize or explain before Yang started shouting. 

“Places, everyone! Ruby, get to costumes!”

Nice work, Casanova, Oscar thought as Ruby hurried off, if this wasn’t going to be awkward enough.

* * *

** “Quiet on the set!” ** Yang shouted through a megaphone.

** “And…ACTION!!!” **

The door to the set opened and Ruby crept into the fake bedroom.

“Grandma,” she said in a faux-innocent voice, “I’m here!”

“I…I’m in the bedroom.” Oscar said. The script had said to use a fake old lady voice but Oscar had completely forgotten until after he’d said the line

“You know, the innocent angle might actually work for us here.” Oscar heard Yang whisper.

When Ruby skipped over to the side of the bed, Oscar could see what she was wearing. It was less in the sexy range and more in the cute range, with lace and ruffles but why did she have to wear it like a pro!?

“Grandma,” Ruby said, leaning in too close for Oscar’s comfort, “What big eyes you have!”

Was she wearing perfume? Was it cherry and rose scented?

“A-all the better to…to see you with…”

He swallowed. He was sure that right now he had the on-camera charisma of a pet rock. But backing out meant a disappointed aunt, so he might as well soldier on.

“My dear.”

If Ruby noticed the tremor in her voice, she gave no sign of it.

“And Grandma, what big ears you have!”

“All the better to hear you with.”

He hoped that nobody would notice how he didn’t add ‘my dear’ to that last line. He had like fifteen minutes alone with the script, so he hoped the crew would cut him a break.

“And Grandma…”

Here it comes, Oscar thought, the most embarrassing part of the script. Whoever wrote it deserves to be dipped in batter and deep fried! Ruby gripped the bed covers and Oscar braced himself.

“What a big…”

The moment the covers came off, Oscar fought down the urge to cover himself. No one’s going to see this, he told himself. When it’s over and they’ve given him a copy, he would find a dark place in the woods, bury it, and then never speak of this again. And from the expression on Ruby’s face, Oscar thought she’d appreciate that course of action.

“Oh…”

Oh? What was oh? Was that a good ‘oh’ or a bad ‘oh’?

“Oh my…”

What was she doing? Right now, she was just looking confused.

“That…that is a big cock.”

“What?”

Oscar looked down at himself. He’d always thought he was normal sized.

“I just…”

Ruby put hand on her head and chuckled.

“I kind of wish I could take a picture.”

Oscar sat up, intrigued by his co-star’s change in demeanor.

“Really?”

“Uh-huh. I didn’t know what I was expecting when we had that contest, but whoa!”

“Well, is it…is this okay?” Oscar asked hesitantly, shifting in his seat, “if you don’t want to do this, I get it.”

An amused smile turned up the right side of Ruby’s mouth.

“That’s sweet of you, but don’t worry. I’ve got enough talent for both of us.”

“Oh. Well that’s probably good, because…”

Oscar steeled himself. Of all the ways he could have pictured admitting this to a girl, this wasn’t one of them.

“Because it’s…”

He said it quietly, hoping he wouldn’t have to repeat it. Ruby frowned.

“What was that?”

He repeated it, only slightly louder.

“One more time.”

“ I said…it’s…it’s my first time.”

For a moment, Ruby stared at him, and Oscar feared the worst. Before he could calculate where this situation fell on a scale of one to dying from embarrassment, Ruby covered her eyes and squealed loud enough to make Oscar jump.

“What!? What is it?”

“You’re just…so cute! With your wolf ears and your blushing and your big cock and…”

“This isn’t in the script but it is GOLD!” Yang whispered from offset.

Or at least Oscar thought that’s what he heard Yang say, but he was still hooked on what Ruby had called him.

Cute? Well, that was a boost to his self-confidence. It wasn’t every day a woman complimented your anatomy and said you were cute in the same conversation.

“Well, while we’re being honest,” said Oscar, “I’ve had a crush on you for a while now.”

Ruby blushed and fidgeted and Oscar’s heart went pitter pat.

“Oh really?”

“Yeah. I watch your interviews and read articles about you and I…um…

“It’d be a lie if I didn’t tell you I never… caught myself thinking about him when I shouldn’t.”

“Oh?”

Ruby crawled onto the bed, leaning forward into his personal space and Oscar felt his throat tighten, but in a good way.

“Then, what kinds of things does Mister Wolf think about Little Red?”

For a moment, Oscar’s mind went blank before a laugh finally burst from his throat, a laugh which Ruby caught.

“We’re not exactly staying in character here.” Ruby chuckled.

“It’s not going to be released anyway.” Oscar said.

Ruby smirked, her lips a hair’s breath away from the left side of his mouth.

“Well in that case…”

** “WE’VE RENTED THIS PLACE FOR A LITTLE OVER TWO HOURS!” ** Yang shouted through her bullhorn, ** “LET’S SEE SOME ACTION!” **

That was certainly a mood killer. Couldn’t that director just leave the cameras running and buzz off? It’s not like this was going to make anyone any money.

“I’m gonna do it!”

Oscar turned to the sound of Ruby’s voice. His co-star had a look of iron resolve on her face.

“I’m gonna give you the ride of your life!”

Before he could respond, Ruby tackled him onto the mattress, smashing their lips together. Oscar’s mind, meanwhile, was reeling, not able to form a cohesive question, let alone think through the sensations this girl on top of him was sending by running her hands up and across his exposed skin. Maybe he didn’t have anything to worry about…


End file.
